


An Exploration of Flawless Imperfection

by iamee



Category: Teen Wolf (TV)
Genre: Anal Fingering, Anal Sex, Barebacking, Derek Hale is Bad at Feelings, Derek and Stiles are Mates, Established Relationship, First Time, Fluff and Smut, Humor, Loss of Virginity, M/M, Plot What Plot/Porn Without Plot, Power Bottom Stiles, The Author Regrets Nothing, They are Both Dorks, Top Derek, Topping from the Bottom
Language: English
Status: Completed
Published: 2014-06-22
Updated: 2014-06-22
Packaged: 2018-02-05 18:52:46
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 2,422
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1828579
Author URL: https://archiveofourown.org/users/iamee/pseuds/iamee
Summary: <blockquote class="userstuff">
              <p>Stiles may be the virgin, but Derek is the one who completely loses it.</p>
            </blockquote>





	An Exploration of Flawless Imperfection

**Author's Note:**

  * For [caylar](https://archiveofourown.org/users/caylar/gifts).



> (I love you, Jimmy.)
> 
> Uhm, yes. I have this headcanon that Stiles would need to comfort Derek during their first time. So I wrote PWP with emotions. Enjoy.

**An Exploration of Flawless Imperfection**

 

Uh, Stiles said. My knowledge on the subject is kinda limited, but I think you're supposed to breathe.

 

Derek gave a sound that was pretty much a pathetic howl if there was such a thing. At least there was the indication of air filling his lungs. Which was a success, as far as Stiles was concerned.  
He moved a little, trying to adjust himself on top of Derek and press a kiss just underneath his collarbone. It wasn't the most ideal of positions to be fingered (again: at least in his very very limited experience), but it was the only one they could have agreed on. "Agreed on" meant in this case it was the only position in which Derek's eyes flashed less and his nails stayed kinda blunt which Stiles preferred given their current location thankyouverymuch.

 

Derek.

 

All it got him was Derek's eyelids fluttering and his lips parting, pink tongue wetting them like the sight wasn't totally obscene and kinda maddening. Fucking useless sexy werewolf boyfriend.

 

Fine. I'll just do all the work then.

 

Stiles rolled his eyes and pushed himself up enough to sit back, biting back a gasp when it drove Derek's fingers deeper inside and for a moment he just rocked back and forth. Fuck yes. Another time he'd tell Derek how good that was, how stupidly, amazingly good to have his fingers drag over his walls. Right now it would most likely result in this ending too soon and Stiles had not waited for **months** just to give up within touching distance of the finish line, goddamnit.  
So he moved up a little, fingers nearly leaving him and he bit his lip as he reached for the lube. Derek finally cracked an eye open. 

 

Decided to join me? 

 

Stiles made a mental note to work on his bedroom voice. More sensual confidence and less passive-aggressive neediness would be sort of nice.

 

Stiles... 

 

Another eye opened, Derek's breath coming in short, warm surges, like it actually wasn't possible to keep it down long enough. 

 

You know, we don't really have to do this.

 

What?

 

The shock on Derek's face almost made him laugh until it turned into something frightened, wordless, and Stiles swallowed.

 

I mean I want to, I do. But you...

 

Derek repeated his name, pushing himself up so they were both sitting, cocks rubbing together, mouths finding each other and yes. God yes. That was it, their skin sticking together with sweat and precome, their tongues curling around little curses, their hands tangling into hair and sheets, their...  
Derek _whimpered_.

In theory, Stiles' plan had been rather flawless. Pretty much perfect, to be honest.

 **Step 1:** Have a parent-free house for a night.  Check.  
 **Step 2:** Buy condoms and lube in a way Scott doesn't notice because you don't want to have that conversation with your best friend.  Semi-check.  
 **Step 3:** Get Derek naked.  Check. Definitely check.  
 **Step 4** : Find inner calamity in the fact that your older, more experienced boyfriend has obviously done more than simply have a research-based three-weeks-long gay porn marathon. Check???

Like he had said: flawless in theory.

 

Derek. 

 

Stiles took a deep breath.

 

Virgin Enterprise to Planet Derek. _I'm_ the one who's supposed to have a minor freak-out about getting my cherry popped. _You_ (here he pressed a kiss to Derek's lips) are supposed to tell me it's going to be okay when you put your fantastic dick inside me. 

 

I'm... sorry.

 

What was that?

 

Stiles pulled back enough to study Derek's face, relieved to find him looking back until he saw the way his pupils were dilated, eyes near black, with just the smallest circle of green around them. And uh... was that because of _him_?

 

I know, Derek said. He sounded absolutely raw. I know I should be, I should... but fuck. St _iles_.  


 

From somewhere inside Stiles' guts warmth spread out throughout his whole body, even stronger than when they had started. He was doing this to Derek. He was making him forget all that big bad wolf bullshit (as hot as that was). He was... apparently making him shiver, if the tremble going through Derek's arms and ending in this abdomen where they were still pressed together, slick and hot, was any indication at all. Jesus Christ. 

 

Shh, Stiles found himself whispering against Derek's lips. I've got this.

 

And for the moment it felt like it was true, at least when he squeezed more lube into his hand and sank back on Derek's fingers, eliciting a strangled moan from probably more than one of them. 

 

It'll be okay.

 

His slick fingers wrapped around Derek's length, the tips brushing his own cock and his hips bucked in tandem with Derek's. It went on for a bit in silence, just their breaths and the wet sound of skin on skin filling the room. It was heady, it wasn't enough, it was good _good_ good, but mostly because there was more to come.

 

Stiles, Derek said again. For the uncounted time that night.

 

Yeah. Please.

 

Their foreheads leaned together, his hand leaving Derek's cock in favour of reaching behind himself, to where Derek's fingers curled inside of him. Thank fuck that the part of Derek's brain which was responsible for preparation hadn't been fried with the rest of it. Stiles knew better than to be ungrateful for the small things.

 

Just lemme...

 

He drew a breath, one finger dipping inside himself, joining Derek's three, awkward angle be damned. It had its undeniable benefits to be good with improvising.  
Derek's lips parted for a shuddering breath, followed by a sound that totally not made Stiles' cock twitch between them. There was a tongue ghosting over his bottom lip, and seriously, had Derek stopped shaking only once since he had noticed? God, he was so screwed. Hopefully.

 

I think I'm ready.

(Understatement of the year.)

 

He didn't imagine the nod Derek gave him, or the way he gripped his finger when they both withdrew from his body, like he needed to hold onto any part that was Stiles, any reminder that this was really happening.

Another kiss, a little push and Derek was splayed out on the bed, chest heaving, his eyes hooded. Even if Stiles had wanted he couldn't be mad because come on, Derek fucking Hale was in his bed, turning out to be pure submission under his virgin hands. There you go with a turn-on he didn't think existed. 

 

So uhm. 

 

Stiles slid up on Derek's body, heart pounding and blood rushing in his ears. Because _this_ was _it_. 

 

How about we skip condoms? It's not like werewolves have diseases, right? And I'm like, one hundred percent untouched. Well, not untouched, you know what I mean. You were there every time I _was_ touched and that makes it pretty much – 

 

Stiles.

 

That. That finally sounded like the Derek he knew, growly and with this hint of annoyance like he couldn't quite figure out why he was enjoying Stiles' company oh so very much and it never ceased to bug him. 

 

Yes?

 

Are you going to make me beg?

 

Stiles considered that for a moment, hands on Derek's chest and their gazes locked. The moment stretched. The expression in Derek's eyes became slightly panicked.

 

No.

 

Derek let out a breath, his head falling back into the sheets, a deep rumble going through him and vibrating in Stiles' body.

 

Then...

 

I mean "no, not today". But I definitely like the thing your face just did.

 

I hate you.

 

Stiles felt a grin tugging at the corner of his mouth as he reached behind himself and guided Derek to his entrance, amazingly enough somehow managing not to lose his balance.

 

No, you don't.

 

There was a bit of grinding involved, the shifting of his hips, the straightening of his spine, and more than just one wilful struggle to get his body to relax. But eventually the head slipped in, and Stiles stilled, trying to catch his breath.

In the warm glow of his bedside lamp, Derek's skin became the most amazing thing. Under his hands, Derek's heart beat like it was going to break free from his ribs. Under his gaze, Derek opened his eyes once again and they were wet with something so desperate that Stiles had to lower his head and suck in the heavy-scented air between them.

A million things he wanted to say, all stupid and needy and hopelessly in love, but all that found its way onto the tip of his tongue was Derek's name (and how cliché was that?) when he sank further down on him. Inch. By fucking. Inch.

It was quiet now, minus their barely controlled panting and the small hissing sound Stiles gave now and then, when the pressure became too much, forcing him to pause, breathe through it and continue. Because stopping wasn't an option he'd even consider.

Endless seconds later, his heart hammering somewhere in his ears and his hands having gripped Derek's shoulders, he was flush against his hips. Nothing, not even a sheet of paper would have fitted between their bodies, but **they** fitted together perfectly, snug and hotdeep _rightthere_. And nothing, no amount of porn or his admittedly pretty vivid fantasy could have prepared him for the noise Derek made, the first time he started moving. Because Derek sounded absolutely _wrecked_.

And holy animal crackers, could Stiles ever sympathise with that. Derek pressed to his insides in a way that would ruin fingers for him for a while. Hell, it would probably ruin _him_ while he was on it. When he moved, there was a slight burn, but mostly a thick drag over his walls, right up against his prostate, and by the third time he was crying out something that was hopefully not as obscene as the thoughts dancing through his endorphine-attacked brain.

 

M _or_ e.

 

If Stiles had had the energy he would have mentally patted himself on the shoulder for managing an entire _whole_ complete word, but the way it was right now, he was more than happy to roll his hips and dig his fingers into Derek's shoulders on every downward movement. And then Derek met him halfway.

 

_Fuck!_

 

Stiles' eyes flew wide open, his mouth probably curved into a dumbstruck "oh"-shape, his hands slipping to Derek's neck so he could pull himself down, whimper against his lips instead of the ceiling. His thighs squeezed tighter around Derek's hips, a sob rolling from his lips when Derek pulled up his knees and thrust into him with the newly gained leverage, that bastard.  
Fuck indeed.

A kiss was clumsily brushed to the corner of his mouth, hands curling around his hipbones and pulling him down every time Derek slammed back in. So much for holding back.

 

Derek!

 

His heart had seemingly made the decision to escape through his throat, because by now it was blocking his breathing, his skin growing tighter with every passing second. Every. Goddamn. Thrust. Right to the core of this body. Behind closed eyelids, colours flashed, each push jolting through his body a mixture of pleasure and pain. He would doubtlessly develop a temporary aversion to the concept of "sitting down" over the next few days. 

And as for Derek... Derek was whining, no matter how precisely he drove back into Stiles' all too welcoming body, as if they had reached a level of sheer unbearable intensity where there was nothing they could do but follow the pulls and pushes of their bodies. And maybe that was true. It certainly felt like it was true.

 

I've... got you, Stiles gasped.

 

His hands moved up to cradle Derek's face, their noses rubbing together from the frantic movement of their hips. Once upon a time there had been oxygen in Stiles' bedroom but it had long been replaced with a dense fog of sweat and hormones, lube and something that was just _them_.

And Derek's hand slid between them, into the space between their bellies, where everything was slippery and intoxicating, fingers wrapping around Stiles' cock, starting to stroke him like it wasn't even consciousness, but instinct that told Derek to give back, to make them come as close together as they could.

 

It's okay. It's _oh_..kay.

 

Stiles didn't know what he was saying, why he was still talking, reassuring Derek of stuff he didn't know the first thing about, reminding him that they were fine, alive, here, together. His mouth tasted like metal and sweetness and his hips moved on their own, pushing back at Derek in increasingly sloppy motions. 

They were here and there was nothing else. Nothing but Derek's body all around him, inside of him, taking him apart. Nothing but Derek's sounds, like it was almost painful, like he was losing part of himself in Stiles but loving every second of it. If anything they could ruin each other, shatter to pieces and pick them up again like they always would. Because this was them and this was what they did. The liquid fire in Stiles' belly had long enough been contained, but now it was boiling up, rushing through him with force and he buried his face in the crook of Derek's neck, stifling a scream as he came over his fingers, pulsing and his thighs quivering from the effort to hold him up.

He felt himself growing tense, incredibly tight around Derek's cock and Derek arched underneath him, hips pressed up against his backside, one shaking hand on the small of Stiles' back. He had never known his name could sound like that, like a plea and a curse and love, and Derek moved inside of him a last time before he stilled. Stiles' lips were parted over Derek's skin, dampening it with breath, eyes half-closed while Derek's come filled him, hot and slick, unlike anything else he'd felt before.

It took a long time until Stiles felt he could safely use his voice again. 

 

I hate to be that guy but if you don't carry me to the bathroom right now, I'll just sleep on top of you. Like this. And then I'll probably stick to you for the rest of our lives and you'll never ever get rid of me. Ever.

 

There was moment of silence before Derek cleared his throat.

 

Shut up, Stiles.

 

The restrained laugh that went through Derek's body felt even better with their bodies still connected and Stiles blinked up at him, a slow grin spreading on his face.

 

Welcome back.

 

 

**The End**


End file.
